Shelter Island Vacations

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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Mashomack Preserve.

Find hotels in Menantic Creek

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩788,234 per night from May 18 to May 19
₩788,234
₩1,080,667 total
May 18 - May 19
includes taxes & fees
8.4/10 Very Good! (778 reviews)
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!

Reviewed on May 11, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩222,560 per night from May 25 to May 26
₩222,560
₩283,116 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (1,343 reviews)
Cute place great views would go back in the summer

Reviewed on May 11, 2026

Montauk Manor
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
The price is ₩292,552 per night from May 13 to May 14
₩292,552
₩502,235 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Unhinged wacko

Reviewed on May 6, 2026

Montauk Yacht Club
See all 4,782 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.